Bovine Metabolome Database: Showing metabocard for 6-Hydroxydopamine (BMDB0001537)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:21 UTC

Update Date

2020-05-11 20:53:28 UTC

BMDB ID

BMDB0001537

Secondary Accession Numbers

BMDB01537

Metabolite Identification

Common Name

6-Hydroxydopamine

Description

6-Hydroxydopamine, also known as 6-OHDA or oxidopamina, belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. Based on a literature review a significant number of articles have been published on 6-Hydroxydopamine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4,5-Trihydroxyphenethylamine	ChEBI
6-OHDA	ChEBI
Hydroxydopamine	ChEBI
Oxidopamina	ChEBI
Oxidopaminum	ChEBI
Topamine	ChEBI
5-(2-Aminoethyl)-1,2,4-benzenetriol	HMDB
6-Hydroxy-dopamine	HMDB
Oxidopamine hydrochloride	MeSH, HMDB
Oxidopamine hydrobromide	MeSH, HMDB
6 Hydroxydopamine	MeSH, HMDB
Hydrochloride, oxidopamine	MeSH, HMDB
Hydrobromide, oxidopamine	MeSH, HMDB
6-Hydroxydopamine	ChEBI
Oxidopamine	MeSH

Chemical Formula

C₈H₁₁NO₃

Average Molecular Weight

169.1778

Monoisotopic Molecular Weight

169.073893223

IUPAC Name

5-(2-aminoethyl)benzene-1,2,4-triol

Traditional Name

hydroxydopamine

CAS Registry Number

1199-18-4

SMILES

NCCC1=C(O)C=C(O)C(O)=C1

InChI Identifier

InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2

InChI Key

DIVDFFZHCJEHGG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Catecholamines and derivatives

Alternative Parents

Substituents

Catecholamine
Hydroxyquinol derivative
Phenethylamine
2-arylethylamine
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Polyol
Amine
Hydrocarbon derivative
Primary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amino compound (CHEBI:78741 )
catecholamine (CHEBI:78741 )
benzenetriol (CHEBI:78741 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	232 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.91	ALOGPS
logP	-0.15	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.23 m³·mol⁻¹	ChemAxon
Polarizability	17.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-8900000000-ec968317710bfa0af4b1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-8339000000-c3b7e127f97564a22ec0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uk9-0900000000-c39da540b6c679cdf01d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0900000000-f41c773935ebd031beb2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0pdr-4900000000-4462df383c91a9168490	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-1170-9100000000-7e17c8846c48da0e6c28	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2900000000-067de2aeac12b5d386d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pdr-9800000000-93edb759b0db1c672272	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0900000000-d1d46264304355721947	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-1900000000-b2b31af5a8fedb1fe195	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-9400000000-b62782dd6a193e71ac0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-f10baabe2e89652114f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-21109e5bbac363c8a3e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006y-9800000000-a28d8466178b557c9aa7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0900000000-aae03a8148760ccfb8d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ufr-1900000000-69cce15bb35d7f9b2ecf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0q30-9100000000-3ab71c99e27d9e425c1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-e3d8bfd20fe113d52f6a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-98fc147d84fd76661021	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9700000000-74dbc04020f90c44cd02	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adrenal Medulla
Brain
Fibroblasts
Kidney
Liver
Neuron
Spleen

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Medulla	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001537

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022678

KNApSAcK ID

Not Available

Chemspider ID

4463

KEGG Compound ID

Not Available

BioCyc ID

CPD-7666

BiGG ID

Not Available

Wikipedia Link

Oxidopamine

METLIN ID

6307

PubChem Compound

4624

PDB ID

Not Available

ChEBI ID

78741

References

Synthesis Reference

Napolitano, Alessandra; Crescenzi, Orlando; Pezzella, Alessandro; Prota, Giuseppe. Generation of the Neurotoxin 6-Hydroxydopamine by Peroxidase/H2O2 Oxidation of Dopamine. Journal of Medicinal Chemistry (1995), 38(6), 917-22.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 6-Hydroxydopamine (BMDB0001537)

Structure for BMDB0001537 (6-Hydroxydopamine)